This week I spoke with TechCrunch about one facet of distributed work that differs from physical offices — the idea of “office politics.” I can’t claim that distributed work will solve everyone’s personal differences, but I do think it relieves some of the pressures that might come from forced cohabitation and environments that are prone to interruption. They also have some great points from Jason Fried and and Wade Foster.

Prospress joining Automattic

Asides

As you may have read on the WooCommerce blog, Prospress blog, WP Tavern, Post Status, or Techcrunch, the team at Prospress is joining forces with WooCommerce at Automattic to help accelerate the adoption and democratization of ecommerce across the web. Whew that’s a lot of links! Prospress was best known for their extension that allowed many types of Subscriptions on top of WooCommerce, but also has some cool marketing automation and automated testing tools as well. I love that Prospress was already a Five for the Future company, which aligns really well with Automattic’s long-term goals and contributions to the wider community.

Jack Dorsey and Running Two Companies

Podcast

I had the pleasure of interviewing Jack Dorsey for the Distributed podcast, a conversation that ended up going a bit deeper and longer than previous episodes.

In preparation for the interview I kept coming across people critical about the fact that Jack is the CEO of two companies simultaneously, Twitter and Square, each having over 5,000 employees.

I think what people miss is that at that scale, running a company is not that different from running a large division of a company. No one asks Jeff Bezos how he’s CEO of both a retail company and a cloud computing one (AWS), or Tim Cook how he’s CEO of a hardware business and a services business, and of course with both of those examples the breadth of what the companies cover is much wider. Also as an added benefit, shareholders can choose to invest in Square and Twitter together or not.

All of that said, I think having a CEO-level seat at two of the most influential technology companies today does allow for accelerated learning, as organizational experiments will naturally happen at each company and then the best practice can be shared to the other. Jack wasn’t aware how much peer executives at each company meet with each other to share learnings, but that seems like an obvious win.

Readers of this blog will especially appreciate how much we talked about open source and cryptocurrencies, and his view on the three things he’s responsible for as CEO. Give it a listen and let me know what you think.

Sunbird Security Isn’t Nothing

Apple

This might get lost in the OpenAI earthquake happening, but it’s important so I wanted to post about it. (And gosh! A Starship launch, which is amazing. We live in interesting times.) On Tuesday, Nothing, who makes the cleanest and most interesting Android phones (and whose earbuds sound great), announced via my favorite tech video channel, MKBHD, that the phones would support iMessage on Android, so you can be a blue bubble with your friends. This got a lot of pickup!

It got a little buried, though, because on Thursday Apple said it was going to support the RCS standard, which Google and others had been lobbying hard for. However, it’s doing the bare minimum: RCS isn’t actually encrypted, and Apple’s not doing the Google proprietary thing to encrypt it, and so non-Apple people still get green bubbles. (More on that later.)

iMessage on Android (and Windows!) is on the roadmap for Texts, the all-in-one messaging platform Automattic acquired last month. The Texts team is obsessed with security, and that’s part of why the platform is desktop-only right now—to keep everything 100% client-side and fully encrypted in a way that could never be accessed by the team, or have any compromise in the middle, they’ve been taking their time to get the engineering right on the mobile versions. So they poked around the Sunbird app that Nothing partnered with, and it wasn’t pretty. Here’s Texts founder Kishan Bagaria:

The BlueBubbles thing might be a mistake, but seeing the unencrypted data on the wire definitely wasn’t. Sunbird replied and doubled down on Twitter, citing some ISO standard and claiming it was “encrypted.”

Okay! Now you’re caught up to Friday. Texts says Sunbird isn’t secure, Sunbird says it is. He said, she said, right? Not quite—there are receipts. This blog post lays out even more than Kishan tweeted originally and shares code so you can confirm this yourself. tl; dr: Sunbird puts all your iMessages and attachments into Firebase.

What should you take away from this?

Nothing (the company) still makes amazing hardware that you should absolutely check out and use. It’s my favorite Android experience. I think the company got bamboozled by Sunbird, and unfortunately this went mainstream on MKBHD.

Sunbird appears either not to understand security or to lie about it, and probably misled Nothing. I would recommend double-checking what that team claims in the future.

Who should we actually be upset with?

Apple.

You shouldn’t need to jump through all these hoops to have a blue bubble on iMessage. Design can create great things; it can also harm. Apple’s design decisions to “magically” upgrade SMS or texts or RCS into iMessage, which is better and more secure, creates a green-bubble ghetto that’s also a terrible user experience for anyone not on an Apple-made device.

I’ve heard stories of teenagers being ostracized because they couldn’t afford an iPhone, of group chats rejecting people who turn the chat from blue to green. I know that sounds petty, but do you remember middle school? It’s about status, and Apple knows that. Everything they make bleeds status and signaling. They’re the best in the world at it, and I should know—I’m typing this post from a M3 Max black MacBook with 128GB of RAM. But while status signaling with amazing hardware and design touches is harmless, in software and social settings in can be harmful.

Regardless of how it started, today the green bubble indicates cheaper, lower-status, less secure. Apple’s half-hearted support of RCS just continues this. Sunbird (and others) shouldn’t need to jump through so many hoops around this stuff by reverse engineering. Apple should open up iMessage APIs so it can be natively supported just like every other 100M+ messaging platform is: Telegram, Signal, WhatsApp, et al. Teens who can’t afford or don’t want an iPhone should be able to have an app that lets them connect with their friends as peers, securely and with all the features that are easy to support in messaging.

Tim Cook, Apple, we love you. Trillion-dollar company, and lots of room still to grow. Allowing iMessage/FaceTime to interoperate (like it used to!) might take .01% off your growth rate, but it’s the right thing for humanity. Yes, I know Google is shady too, and they’re locked in this smartphone death match with you. But take person-to-person communication out of the struggle, make it a DMZ, and be content to compete in all the other areas you’re currently crushing: design, silicon, Continuity, security, privacy, customer experience, retail stores, spatial audio, the list goes on.

I have no idea how to get in touch with YouTubers, but Marques, if you see this, I’m happy to chat about the future of technology, open source, freedom, and privacy.

Update: As I was writing this, the Nothing Chats app has been pulled from the Play store.

Update 2: From my colleague Batuhan:

Podcast with Texts founder Kishan and Techcrunch

Kishan Bagaria and I had chance to catch up with Alex Willhelm on the Techcrunch Equity podcast, it’s a bit of a time travel since we recorded this on November 28th and there has been a ton of activity in the messaging space including the whole Beeper Mini launch and smackdown from Apple. However it’s worth listening to get to know Kishan and hear some of Automattic’s broader, long-term strategy in this space.

To give our current take with regards to iMessage: Right now we run on desktop only, basically automating Apple’s first-party app. This obviously won’t work on iOS or Android. With every network we support we want to have a good, non-adversarial relationship that puts the user first, with the utmost standards for privacy and security, and understanding the principles and values each network is trying to uphold. We’re watching this space unfold very closely, and trying to help where we can. Check out the episode here:

Proprietary software is like creating art which no-one can see. Open Source elevates software engineering to a collaborative art form. Code is poetry.

— Tom Willmot

Some choice words from Tom Willmot, who was watching Kirby Fergusen’s Everything is a Remix, which I’ll check out now.

Freedom Grants

Audrey

The Audrey Scholars program is still getting started, but I wanted to introduce another opportunity: Freedom grants. As the page says “If you are an open source contributor, and you feel your current political environment is incompatible with open source values, we would like to offer the opportunity for a grant to help you get set up in a new environment. Please state your case below.”

I’m not sure exactly how this will work, but we’ll figure it out together. The offer is out there. This is very much inspired by the work of the Oslo Freedom Forum.

It’s hard to pick a favorite tenor player, but the GOATs that come to mind are Dexter Gordon, Sonny Rollins, John Coltrane, Michael Brecker, and I’m missing people but if I had to pick someone to express the human condition and soul, it would be Joshua Redman. He has such incredible fluency with the horn you get an amazing emotional experience with his vibrations. He’s probably the greatest living tenor saxophonist. He just did a Tiny Desk concert, and the audio and visual capture was impeccable. I watched this full-screen on an Apple XDR and listened with Airpods Max—the chords they’re using, the subtlety of the interactions— the experience was exquisite. (Also peep HSPVA grad Paul Cornish!) I can’t embed because it’s not on Youtube yet.

Illuminate has crossed the funding threshold it needed to actually kick off the project of bringing the Bay Lights back to San Francisco, as Heather Knight writes for the New York Times. The upgraded lights will be visible not just from San Francisco but also in Oakland, Treasure Island, Berkeley… all across the Bay. It’s felt like the lights have been the lumen-physical embodiment of San Francisco’s struggles: sparkling and inspiring at the start, then facing troubles, a trough of darkness, and now hope for something better sparked and on the horizon.

I’d love to get as many citizens and addresses in San Francisco as donors, however small, to round out the last bit of the funding, so that as many people as possible can feel the ownership and pride of making the city better. Back in January when I promoted this last it was on a terrible platform, it’s now been re-done by the GiveWP team to be totally native WordPress and a slick donation experience, easy to do on mobile and with Apple Pay. (Major kudos to Devin Walker there!) Please share the link to your friends, especially ones that see the bridge from their home, for $10 it’s the cheapest pro-social dopamine boost you can have every time you look at the bridge.

We no longer need companies, institutions, or government to organize us. We now have the tools to organize ourselves. We can find each other and coalesce around political causes or bad companies or talent or business or ideas. We can share and sort our knowledge and behavior. We can communicate and come together in an instant. We also have new ethics and attitudes that spring from this new organization and change society in ways we cannot yet see, with openness, generosity, collaboration, efficiency. We are using the internet’s connective tissue to leap over borders—whether they surround countries or companies or demographics. We are reorganizing society. This is Google’s—and Facebook’s and craigslist’s—new world order.

— Jeff Jarvis in the book What Would Google Do? Published 2009.

Interesting to revisit as they float trial balloons on breaking Google up (terrible idea) or other antitrust enforcement.